US4165231AExpiredUtility
2,6-Dinitroaniline herbicides

Assignee: AMERICAN CYANAMID COPriority: Aug 25, 1971Filed: Mar 11, 1977Granted: Aug 21, 1979
Est. expiryAug 25, 1991(expired)· nominal 20-yr term from priority
Inventors:Albert W. Lutz Robert E. Diehl
C07C 205/12C07C 311/39
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Claims
Abstract

The invention is the use of substituted 2,6-dinitroaniline compounds as preemergence herbicides and compositions employing the substituted 2,6-dinitroaniline compounds.
Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A method for the preemergence control of undesirable plant species comprising applying to soil containing seeds of the undesirable plant species a herbicidally effective amount of a compound of the formula: ##STR82## wherein: Y is halogen, alkyl C 1  -C 4 , alkenyl C 2  -C 4 , or CF 3  ; Z is alkyl C 1  -C 4 , alkenyl C 2  -C 4  or monosubstituted alkyl C 1  -C 4  where the substituent is halogen, alkoxy C 1  -C 4  or -NR 3  R 4  ;   R 1  is hydrogen, alkyl C 1  -C 6 , alkenyl C 2  -C 6  or alkynyl C 2  -C 6  ;   R 2  is alkyl C 2  -C 7  (straight, branched or cyclo), alkenyl C 2  -C 6 , alkynyl C 2  -C 6 , or monosubstituted alkyl C 1  -C 4  where the substituent is halogen or alkoxy C 1  -C 4  ; and   R 3  and R 4  each represent hydrogen or alkyl C 1  -C 4  ; with the proviso that when Y and Z are methyl and R 1  is hydrogen or ethyl, then R 2  cannot be ethyl; and that when R 1  is hydrogen and Y and Z are methyl, R 2  cannot be 1-ethylbutyl, 1-ethylpropyl, 1-methylbutyl or 1-methylpropyl.   
     
     
       2. A method according to claim 1, wherein the compound is of the formula: ##STR83## wherein: R 2  is C 3  -C 7  secondary alkyl free from quaternary carbon atoms or monochloro (C 3  -C 4 ) alkyl; Y is CH 3 , C 2  H 5 , C 3  H 7  --n, C 3  H 7  --i, C 4  H 9  --i, sec--C 4  H 9  or Cl, and   Z is --CH 2  OCH 3  or --CH(CH 3 )OCH 3 .   
     
     
       3. A method according to claim 2 wherein the compound is N-(1-ethylpropyl-α 3  -methoxy-2,6-dinitro-3,4-xylidine. 
     
     
       4. A method according to claim 2, wherein the compound is: 4-ethyl-N-(1-ethylpropyl)-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       5. A method according to claim 2, wherein the compound is: N-(1-ethylpropyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       6. A method according to claim 2, wherein the compound is: N-isopropyl-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       7. A method according to claim 2, wherein the compound is: N-sec-butyl-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       8. A method according to claim 2, wherein the compound is: N-sec-butyl-4-ethyl-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       9. A method according to claim 2, wherein the compound is: 4-ethyl-N-isopropyl-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       10. A method according to claim 2, wherein the compound is: 4-ethyl-α-methoxy-N-(1-methylbutyl)-2,6-dinitro-m-toluidine. 
     
     
       11. A method according to claim 2, wherein the compound is: N-(1-ethylbutyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       12. A method according to claim 2, wherein the compound is: 4-sec-butyl-N-(1-ethylpropyl)-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       13. A method according to claim 2, wherein the compound is: N-[1-(chloromethyl)propyl]-7-methoxy-o-cymen-5-amine. 
     
     
       14. A method according to claim 1, wherein the compound is of the formula: ##STR84## wherein: R 2  is C 3  -C 7  secondary alkyl free from quaternary carbon atoms or monochloro (C 3  -C 4 ) alkyl; Y is CH 3 , C 2  H 5 , C 3  H 7  --n, C 3  H 7  --i, C 4  H 9  --i, sec-C 4  H 9 , Cl or CF 3  ; and   Z is CH 3  ; with the proviso that when Y is CH 3 , R 2  represents a member other than sec-butyl, 2-pentyl, 3-pentyl or 3-hexyl.   
     
     
       15. A method according to claim 14, wherein the compound is N-(1-ethylpropyl)-α 4 ,α 4 ,α 4  -trifluoro-2,6-dinitro-3,4-xylidine. 
     
     
       16. A method according to claim 14, wherein the compound is: 4-chloro-n-(1-ethylpropyl)-2,6-dinitro-m-toluidine. 
     
     
       17. A method according to claim 14, wherein the compound is: N-(1-methylpropyl)-α 4 ,α 4 ,α 4  -trifluoro-2,6-dinitro-3,4-xylidine. 
     
     
       18. A method according to claim 14, wherein the compound is: 4-chloro-N-sec-butyl-2,6-dinitro-m-toluidine. 
     
     
       19. A method according to claim 14, wherein the compound is: N-[(2-chloro-1-ethyl)ethyl]-2,6-dinitro-3,4-xylidine. 
     
     
       20. A method according to claim 14, wherein the compound is: N-[(2-chloro-1-methyl)ethyl]-2,4-dinitro-3,4-xylidine. 
     
     
       21. A method according to claim 14, wherein the compound is: 4-ethyl-N-(1-ethylpropyl)-2,6-dinitro-m-toluidine. 
     
     
       22. A method according to claim 14, wherein the compound is: N-(1-ethylpropyl)-4,6-dinitro-o-cymen-5-amine. 
     
     
       23. A method according to claim 1, wherein the compound is of the formula: ##STR85## wherein: Y is CH 3 , C 2  H 5 , i--C 3  H 7 , n--C 3  H 7 , sec--C 4  H 9 , i--C 4  H 9  and Cl; Z is CH 3  or --CH 2  OCH 3  ; and   R 2  is secondary C 3  -C 4  alkyl monosubstituted with methoxy.   
     
     
       24. A method according to claim 23, wherein the compound is N-[1-(methoxymethyl)propyl]-2,6-dinitro-3,4-xylidine. 
     
     
       25. A method according to claim 23, wherein the compound is N-(3-methoxy-1-methylpropyl)-2,6-dinitro-3,4-xylidine. 
     
     
       26. A method according to claim 23, wherein the compound is 4-chloro-N-[1-(methoxymethyl)propyl]-2,6-dinitro-m-toluidine. 
     
     
       27. A method according to claim 23, wherein the compound is N-(2-methoxy-1-methylethyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       28. A method according to claim 23, wherein the compound is N-[1-(methoxymethyl)propyl]-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       29. A method according to claim 23, wherein the compound is N-(2-methoxy-1-methylethyl)-2,6-dinitro-3,4-xylidine. 
     
     
       30. A method according to claim 23, wherein the compound is 4-ethyl-α-methoxy-N-(2-methoxy-1-methylethyl)-2,6-dinitro-m-toluidine. 
     
     
       31. A method according to claim 23, wherein the compound is 4-ethyl-α-methoxy-N-[1-(methoxymethyl)propyl]-2,6-dinitro-m-toluidine. 
     
     
       32. A method according to claim 23, wherein the compound is N-(3-methoxy-1-methylpropyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       33. A preemergence herbicidal composition comprising an admixture of a herbicidal adjuvant and a herbicidally effective amount of a compound of the formula: ##STR86## wherein: Y is halogen, alkyl C 1  -C 4 , alkenyl C 2  -C 4 , or CF 3  ; Z is alkyl C 1  -C 4 , alkenyl C 2  -C 4  or monosubstituted alkyl C 1  -C 4  where the substituent is halogen, alkoxy C 1  -C 4  or --NR 3  R 4  ;   R 1  is hydrogen, alkyl C 1  -C 6 , alkenyl C 2  -C 6  or alkynyl C 2  -C 6  ;   R 2  is alkyl C 2  -C 7  (straight, branched or cyclo), alkenyl C 2  -C 6 , alkynyl C 2  -C 6 , or monosubstituted alkyl C 1  -C 4  where the substituent is halogen or alkoxy C 1  -C 4  ; and   
     
     
       R 3  and R 4  each represent hydrogen or alkyl C 1  -C 4  ; with the proviso that when Y and Z are methyl and R 1  is hydrogen or ethyl, then R 2  cannot be ethyl; and that when R 1  is hydrogen and X and Y are methyl, R 2  cannot be 1-ethylbutyl, 1-ethylpropyl, 1-methylbutyl. 
     
     
       34. A method for the postemergence control of undesirable plant species comprising applying to the plant species a herbicidally effective amount of a compound of the formula: ##STR87## wherein: R 2  is C 3  -C 7  secondary alkyl free from quaternary carbon atoms, monochloro (C 3  -C 4 ) alkyl or secondary alkyl (C 3  -C 4 ) monosubstituted with methoxy; Y is CH 3 , C 2  H 5 , C 3  H 7  --n, C 3  H 7  --i, C 4  H 9  --i, sec--C 4  H 9 , Cl or CF 3  ; and   Z is CH 3 , --CH 2  OCH 3  or --CH(CH 3 )OCH 3 .   
     
     
       35. A method according to claim 34, wherein the compound is: 4-ethyl-N-(1-ethylpropyl)-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       36. A method according to claim 34, wherein the compound is: N-(1-ethylpropyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       37. A method according to claim 34, wherein the compound is: N-isopropyl-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       38. A method according to claim 34, wherein the compound is: N-sec-butyl-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       39. A method according to claim 34, wherein the compound is: N-sec-butyl-4-ethyl-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       40. A method according to claim 34, wherein the compound is: 4-ethyl-N-isopropyl-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       41. A method according to claim 34, wherein the compound is: 4-ethyl-α-methoxy-N-(1-methylbutyl)-2,6-dinitro-m-toluidine. 
     
     
       42. A method according to claim 34, wherein the compound is: N-(1-ethylbutyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       43. A method according to claim 34, wherein the compound is: 4-sec-butyl-N-(1-ethylpropyl)-α-methoxy-2,6-dinitro-m-toluidine. 
     
     
       44. A method according to claim 34, wherein the compound is: N-[1-(chloromethyl)propyl]-7-methoxy-o-cymen-5-amine. 
     
     
       45. A method according to claim 34, wherein the compound is N-(1-ethylpropyl)-α 4 ,α 4 ,α 4  -trifluoro-2,6-dinitro-3,4-xylidine. 
     
     
       46. A method according to claim 34, wherein the compound is: 4-chloro-n-(1-ethylpropyl)-2,6-dinitro-m-toluidine. 
     
     
       47. A method according to claim 34, wherein the compound is: N-(1-methylpropyl)-α 4 ,α 4 ,α 4  -trifluoro-2,6-dinitro-3,4-xylidine. 
     
     
       48. A method according to claim 34, wherein the compound is: 4-chloro-N-sec-butyl-2,6-dinitro-m-toluidine. 
     
     
       49. A method according to claim 34, wherein the compound is: N-[(2-chloro-1-ethyl)ethyl]-2,6-dinitro-3,4-xylidine. 
     
     
       50. A method according to claim 34, wherein the compound is: N-[(2-chloro-1-methyl)ethyl]-2,4-dinitro-3,4-xylidine. 
     
     
       51. A method according to claim 34, wherein the compound is: 4-ethyl-N-(1-ethylpropyl)-2,6-dinitro-m-toluidine. 
     
     
       52. A method according to claim 34, wherein the compound is: N-(1-ethylpropyl)-4,6-dinitro-o-cymen-5-amine. 
     
     
       53. A method according to claim 34, wherein the compound is N-[1-(methoxymethyl)propyl]-2,6-dinitro-3,4-xylidine. 
     
     
       54. A method according to claim 34, wherein the compound is N-(3-methoxy-1-methylpropyl)-2,6-dinitro-3,4-xylidine. 
     
     
       55. A method according to claim 34, wherein the compound is 4-chloro-N-[1-(methoxymethyl)propyl]-2,6-dinitro-m-toluidine. 
     
     
       56. A method according to claim 34, wherein the compound is N-(2-methoxy-1-methylethyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       57. A method according to claim 34, wherein the compound is N-[1-(methoxymethyl)propyl]-7-methoxy-4,6-dinitro-o-cymen-5-amine. 
     
     
       58. A method according to claim 34, wherein the compound is N-(2-methoxy-1-methylethyl)-2,6-dinitro-3,4-xylidine. 
     
     
       59. A method according to claim 34, wherein the compound is 4-ethyl-α-methoxy-N-(2-methoxy-1-methylethyl)-2,6-dinitro-m-toluidine. 
     
     
       60. A method according to claim 34, wherein the compound is 4-ethyl-α-methoxy-N-[1-(methoxymethyl)propyl]-2,6-dinitro-m-toluidine. 
     
     
       61. A method according to claim 34, wherein the compound is N-(3-methoxy-1-methylpropyl)-7-methoxy-4,6-dinitro-o-cymen-5-amine.
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